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New aspects in the reaction of azomethines with cyclic CH-acidic compounds

Neue Aspekte der Reaktion von Azomethinen mit cyclischen CH-aciden Verbindungen

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

Treatment of substituted benzylidene anilines1 a – df with cyclic CH-acidic compounds2a–m in ethanol at room temperature yields in additon/elimination reactions the corresponding arylidene derivatives4 and the 2:1 adducts5. The addition products3, which are formed as intermediates, could not be isolated in any case. The donor/acceptor effect of the substituents on the benzylidene moiety influences to a significant extent the reactivity towards the azomethine carbon.

Zusammenfassung

Bei der Umsetzung der substituierten Benzylidenaniline1 a – f mit den cyclischen CH-aciden Verbindungen2 a – m in Ethanol bei Raumtemperatur erhält man in Additions/Eliminierungsreaktionen die Arylidenderivate4 und die 2:1-Addukte5. Die als Intermediat gebildeten Additionsprodukte3 konnten in keinem Fall isoliert werden. Die Donor-bzw. Acceptorwirkung der Substituenten am Benzylidenrest beeinflußt maßgebend die Reaktivität am Azomethinkohlenstoff.

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Authors and Affiliations

  1. Sektion Chemie, Universität Leipzig, D-O-7010, Leipzig, Federal Republic of Germany

    Lothar Hennig, Mario Alva-Astudillo & Gerhard Mann

  2. Institut für Organische Chemie, Karl-Franzens-Universität Graz, A-8010, Graz, Austria

    Thomas Kappe

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  1. Lothar Hennig
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  2. Mario Alva-Astudillo
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  3. Gerhard Mann
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  4. Thomas Kappe
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Hennig, L., Alva-Astudillo, M., Mann, G. et al. New aspects in the reaction of azomethines with cyclic CH-acidic compounds. Monatsh Chem 123, 571–579 (1992). https://doi.org/10.1007/BF00816851

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  • DOI: https://doi.org/10.1007/BF00816851

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